Does your ideal day in Tuscany include strolling through the cinematic countryside, savoring Chianti-filled meals, and lingering in charming towns? It should. And it absolutely happens. Tuscan days can laze away with no trouble at all. But the reality for most people that travel to Tuscany is that you don’t have unlimited dolce vita time in your schedule. That can call for a little time management – not because you want to run on a too-tight schedule – but because you want to avoid the timetable that the tourists are on.

San Gimignano is a case in point. This walled hill town and its impressive cluster of medieval towers is truly a sight to behold. In fact, most days it seems like every visitor to this part of Italy has hopped on a morning motorcoach to behold it at precisely the same moment. It’s a scene that can easily cancel out the quaint Tuscan vibe you’re looking for.

Stroll with us in Tuscany's beautiful Chianti wine region countryside

Exploring Tuscany’s Chianti Wine Region

When you travel with us to Tuscany, try this instead. Spend a morning walking through the scenic countryside and through vineyards. The views are incredible and you’re likely to spot local workers tying up tendrils or snipping at the clusters to concentrate the flavor of the grapes. Villas and castles are tucked into the hills, and you’ll soak it all in on a curated walk with our expert Italian guide. A glass of perfectly aged red wine? It would be impolite to refuse, so you’ll accept an invitation to a private lunch and tasting. Afterward, enjoy stretching out by the pool at your historic villa before your evening explorations in town.

On tour, you’ll have utterly excellent Tuscan days. And in the company of our well-connected local guide, it gets even better. Late afternoon in San Gimignano, the tired tourists are clustering at the coaches and heading back to Florence. Make your back to town as the evening approaches and those impressive towers are reflecting the setting sunlight. Their long, cool shadows sweep slowly across quiet cobbled streets. Your timing is perfect, so you’ll really experience San Gimignano. Wander at will and linger over dinner at a local trattoria for a true taste of La Dolce Vita!

Explore Tuscany